3-Bromoaniline → 3-Bromophenylhydrazine hydrochloride

HRID 1696472Notes

Reaction equation

HRID 1696472 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[N:9]([O-])=O.[Na+].O.O.[Cl:15][Sn]Cl>Cl>[ClH:15].[Br:1][C:2]1[CH:3]=[C:4]([NH:5][NH2:9])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 61436Stannous chloride dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 337573-Bromophenylhydrazine hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of 3-bromoaniline (17 g, 0.1 mol) in conc. HCl (200 mL) was added an aqueous solution (20 mL) of NaNO2 (7 g, 0.1 mol) at 0° C. and the resulting mixture was stirred for 1 h. A solution of SnCl2.2H2O (45 g, 0.2 mmol) in conc. HCl (500 mL) was then added at 0° C. The reaction solution was stirred for 2 h at RT. The precipitate was filtered and washed with EtOH and ether to yield (3-bromophenyl)hydrazine hydrochloride as a white solid, which was used for the next reaction without further purification

Workup

  1. stirringThe reaction solution was stirred for 2 h at RT
  2. filtrationThe precipitate was filtered
  3. washwashed with EtOH and ether

Sources & evidence

ORD record
ord-9d1365d0f39c4414af3c56b59379a3f4
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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